Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and ­Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds

Fatemeh Tamaddon; Farzaneh Pouramini

doi:10.1055/s-0033-1340986

Synlett, Table of Contents

Synlett 2014; 25(08): 1127-1131
DOI: 10.1055/s-0033-1340986

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Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds

Fatemeh Tamaddon*

Department of Chemistry, Faculty of Science, Yazd University, Yazd 89195-741, Iran Fax: +98(351)8210644 Email: ftamaddon@yazduni.ac.ir

,

Farzaneh Pouramini

Department of Chemistry, Faculty of Science, Yazd University, Yazd 89195-741, Iran Fax: +98(351)8210644 Email: ftamaddon@yazduni.ac.ir

› Author Affiliations

Abstract

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Abstract

Selective hydration of nitriles to primary amides as well the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H₂O–EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives.

Key words

hydration - nitriles - amides - quinazolinones - Amberlyst A26 OH - recyclable catalyst

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References

References and Notes

1a Sartori G, Maggi R. Chem. Rev. 2010; 113: PR1
1b Jafari AA, Amini S, Tamaddon F. J. Appl. Polym. Sci. 2012; 125: 1339
1c Zolfigol MA. Tetrahedron 2001; 57: 9509
1d Zolfigol MA, Salehi P, Shiri M, Faal Rastegar T, Ghaderi A. J. Iran. Chem. Soc. 2008; 5: 490

2a Marigo M, Bertelsen S, Landa A, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 5475
2b Sheldon RA. Wallau M, Arends IW. C. E, Schuchardt U. Acc. Chem. Res. 1998; 31: 485
2c Lempers HE. B, Sheldon RA. J. Catal. 1998; 175: 62

3a Sharma M, Pandey S, Chauhan K, Sharma D, Kumar B, Chauhan PM. S. J. Org. Chem. 2012; 77: 929
3b Bozell JJ, Petersen GR. Green Chem. 2010; 12: 539

4a Hattori H. Chem. Rev. 1995; 95: 537
4b Tamaddon F, Tayefi M, Hosseini E, Zare E. J. Mol. Catal. A: Chem. 2013; 366: 36

5a Tamaddon F, Nasiri A, Farokhi S. Catal. Commun. 2011; 12: 1477
5b Tamaddon F, Khoobi M, Keshavarz E. Tetrahedron Lett. 2007; 48: 3643
5c Tamaddon F, Sabeti MR, Jafari AA, Tirgir F, Keshavarz E. J. Mol. Catal. A: Chem. 2011; 351: 41
5d Tamaddon F, Tavakoli F. J. Mol. Catal. A: Chem. 2011; 337: 52
5e Tamaddon F, Kargar-Shooroki H, Jafari AA. J. Mol. Catal. A: Chem. 2013; 368-369: 66
5f Tamaddon F, Moradi S. J. Mol. Catal. A: Chem. 2013; 370: 117

6a Tamaddon F, Moazeni Bistgani J. Synlett 2011; 2947
6b Tamaddon F, Farahi M. Synlett 2012; 23: 1379
6c Tamaddon F, Amrollahi MA, Sharafat L. Tetrahedron Lett. 2005; 46: 7841
6d Tamaddon F, Razmi Z, Jafari AA. Tetrahedron Lett. 2010; 51: 1187
6e Tamaddon F, Razmi Z. Synth. Commun. 2011; 41: 485
6f Tamaddon F, Amirpoor F. Synlett 2013; 24: 1791

7 Mukhopadhyay C, Kumar Tapaswi P. Catal. Commun. 2008; 9: 2392
8 Greluk M, Hubicki Z. Desalination 2011; 278: 219
9 Singh AK, Rita P. Microchem. J. 1991; 43: 112
10 http://www.sigmaaldrich.com/catalog/search/ProductDetail /ALDRICH/542571.
11 Ilgen O, Akin AN, Boz N. Turk. J. Chem. 2009; 33: 289
12 Vicente G, Coteron A, Martinez M, Aracil J. Ind. Crop. Prod. 1998; 8: 29
13 Girolamo MD, Marchionna M. J. Mol. Catal. A: Chem. 2001; 177: 33
14 Girolamo M, Lami M, Marchionna M, Sanfilippo D, Andreoni M, Maria A, Galletti R, Sbrana G. Catal. Lett. 1996; 38: 127
15 Serra-Holm V, Salmi T, Multamäki J, Reinik J, Mäki-Arvela P, Sjöholm R, Lindfors LP. Appl. Catal., A 2000; 198: 207

16a Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown ML. J. Med. Chem. 2008; 51: 4620
16b Connolly DJ, Cusack D, OSullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
16c Abbas SE, Awdallah FM, Ibrahim NA, Said EG, Kamel GM. Eur. J. Med. Chem. 2012; 53: 141

17a Suresha GP, Suhas R, Kapfo W, Gowda DC. Eur. J. Med. Chem. 2011; 46: 2530
17b Pal M. Synlett 2009; 2896

18a Abdel-Jalil RJ, Voelter W, Saeed M. Tetrahedron Lett. 2004; 45: 3475
18b Gao J, He L.-N, Miao C.-X, Chanfreau S. Tetrahedron 2010; 66: 4063
18c Gao L, Ji H, Rong L, Tang D, Zha Y, Shi Y, Tu S. J. Hetrocycl. Chem. 2011; 48: 957

19a Hazarkhani H, Karimi B. Tetrahedron 2003; 59: 4757
19b Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M. Tetrahedron Lett. 2005; 46: 7051
19c Yavari I, Beheshti S. J. Iran. Chem. Soc. 2011; 8: 1030

20a Mizuno T, Ishino Y. Tetrahedron 2002; 58: 3155
20b Rostami A, Tavakoli A. Chin. Chem. Lett. 2011; 22: 1317
20c Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W. Tetrahedron Lett. 2008; 49: 3814
20d Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H. Tetrahedron Lett. 2003; 44: 3199
20e Zhang L, Li J, Yang X, Shi D, Chen J. Acta Crystallogr., Sect. E: Struct. Rep. Online 2008; 64: 450; part 2
20f Zhang LJ, Yu JL, Wang WL, Li H, Xu DD, Bi YD, Liu FD. Tetrahedron Lett. 2014; 55: 710
20g Kidwai MP. Indian J. Chem., Sect. B.: Org. Chem. Incl. Med. Chem. 2008; 47: 1876

21a Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606
21b Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
21c Mansour lakouraj M, Bahrami K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999; 38: 974
21d Gadge ST, Bahange BM. Synlett 2014; 25: 85
21e Subramanian T, Pitchumani K. Catal. Commun. 2012; 29: 109

22a Van Dorsser W, Barris D, Cordi A, Roba J. Arch. Int. Pharmacodyn. Ther. 1983; 266: 239
22b Pevarello P, Bonsignori A, Dostert P, Heidempergher F, Pinciroli V, Colombo M, McArthur RA, Salvati P, Post C, Fariello RG, Varasi M. J. Med. Chem. 1998; 41: 579
22c Ghidini E, Delcanale M, De Fanti R, Rizzi A, Mazzuferi M, Rodi D, Simonato M, Lipreri M, Bassani F, Battipaglia L, Bergamaschi M, Villetti G. Bioorg. Med. Chem. 2006; 14: 3263

23 General Procedure for the Synthesis of 2-Substituted 2,3-dihydro-4(1H)-quinazolinones Amberlyst A26 OH (0.11 g) was added to a solution of 2-aminobenzonitrile (1 mmol) and the requisite benzaldehyde (1 mmol) in EtOH–H₂O (0.5 mL). The reaction mixture was stirred at 50–60 °C for the specified period of time as indicated in Table 2, and the progress of the reaction was followed by TLC. After the completion reaction, the mixture was diluted with hot EtOH and filtered to remove the catalyst. The desired products were isolated by addition of H₂O and filtration of the precipitate. To check the regenerability of Amberlyst A26 OH from the model reaction of 2-aminobenzonitrile with benzaldehyde, Amberlyst was removed after reaction completion by dispersing the reaction mixture in warm EtOH or EtOAc and filtering the reaction mixture. To remove impurities and regeneration of the filtered resin, it was washed with EtOAc, distilled H₂O, and 0.1 M NaOH and dried at r.t.
24 General Procedure for Synthesis of Primary Amides Amberlyst A26 OH (0.11 g) was added to a suspension of the nitrile (1 mmol) in EtOH–H₂O (0.5 mL). The reaction mixture was stirred at 50–60 °C, and the progress of the reaction was followed by TLC. After the completion of reaction, the mixture was diluted with acetone or EtOAc and filtered to remove the catalyst. The desired products were isolated by evaporation of the EtOAc or addition of H₂O and filtration of the precipitate. Selected Spectroanalytical Data for Products 2-(Phenyl)-2,3-dihydro-4(1H)-quinazolinone (Table 3, Entry 1) White solid; mp 219–222 °C; yield: 93%. FTIR (KBr): ν_max = 3302 (NH), 3055 (CH), 1655 (C=O) cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 4.40 (br s, 1 H, NH), 5.85 (br s, 1 H, CH), 6.60–6.70 (m, 2 H, H_arom), 6.95–7.10 (m, 1 H, H_arom), 7.20–7.38 (m, 4 H, H_arom), 7.58–7.78 (m, 2 H, H_arom), and 7.94 (d, J = 10 Hz, 1 H, NH) ppm. ¹³C NMR (125 MHz, CDCl₃): δ = 72.5, 119.5, 119.8, 122.6, 132.1, 132.5, 132.6, 132.8, 138.5, 145.8, 152.9, 169.6 ppm. 2-(Pyridin-3′-yl)-2,3-dihydroquinazolin-4(1H)-one (Table 3, Entry 11) White solid; mp 189–192 °C (lit.^3a 190–192 °C); yield: 92%. FTIR (KBr): ν_max = 3310 (NH), 3065 (CH), 1660 (C=O), 1612 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 5.90 (s, 1 H, NH), 6.65 (d, J = 8.0 Hz, 1 H, CH), 6.81 (t, J = 7.9 Hz, 1 H, H_arom), 7.23–7.38 (m, 3 H, H_arom), 7.77 (dd, J ₁ = 7.8 Hz, J ₂ = 1.5 Hz, 1 H), 7.93–7.99 (m, 1 H, NH), 8.53 (dd, J ₁ = 4.8 Hz, J ₂ = 1.5 Hz, 1 H), 8.6 (s, 1 H) ppm. ¹³C NMR (125 MHz, CDCl₃): δ = 69.5, 117.5, 118.7, 119.8, 122.6, 128.5, 131.6, 138.2, 139.5, 140.8, 151.5, 151.9, 153.9, 169.6 ppm. 1′H-Spiro[cyclohexane-1,2′-quinazolin]-4′(3′H)-one White solid; mp 225–227 °C; yield: 90%. FTIR (KBr): ν_max = 3305 (NH), 3065 (CH), 1665 (C=O) cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 1.48–1.68 (m, 6 H), 1.85 (br s, 4 H), 4.40 (br s, 1 H, NH), 6.43 (s, 1 H, NH), 6.66 (d, J = 5.2 Hz, 1 H), 6.82 (t, J = 5.2 Hz, 1 H), 7.28–7.35 (m, 1 H), 7.87 (dd, J ₁ = 7.5 Hz, J ₂ = 1.0 Hz, 1 H) ppm. ¹³C NMR (125 MHz, CDCl₃): δ = 24.0, 26.8, 39.7, 70.5, 117.0, 119.0, 120.8, 130.4, 136.2, 148, 167.0 ppm. Benzamide (Table 4, Entry 3) White crystals; mp 129–131 °C (lit.^25a 129 °C); yield: 91%. FTIR (neat): ν_max = 3369, 3171, 1657 cm^–1. ¹H NMR (250 MHz, CDCl₃): δ = 6.15 (s, NH₂, 2 H), 7.46 (t, J = 6.0 Hz, 1 H), 7.55 (t, J = 6.0 Hz, 2 H), 7.83 (d, J = 6.0 Hz, 2 H, Ph) ppm. Nicotinamide (Table 4, Entry 6) White crystals; mp 129–131 °C (lit.^25b 131 °C); yield: 94%. FTIR (neat): ν_max = 3275, 3410, 1601 cm^–1; ¹H NMR (250 MHz, DMSO-d ₆): δ = 7.47 (t, J = 5.0 Hz, 1H), 7.59 (s, 2 H, NH₂), 8.18 (d, J = 5.0 Hz, 1 H), 8.67 (d, J = 5.0 Hz, 2 H, Ph), 9.00 (s, 1 H) ppm. ¹³C NMR (62.5 MHz, DMSO-d ₆): δ = 123.9, 130.1, 135.6, 149.1, 152.3, 166.9 ppm.

25a Sahnoun S, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. Tetrahedron Lett. 2012; 53: 2860
25b Khalafi-Nezhad A, Mokhtari B, SoltaniRad MN. Tetrahedron Lett. 2003; 44: 7325

Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and ­Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds

Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds